Cargando…

Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020)

[Image: see text] The tetrahydroisoquinoline (THIQ) natural products constitute one of the largest families of alkaloids and exhibit a wide range of structural diversity and biological activity. Ranging from simple THIQ natural products to complex trisTHIQ alkaloids such as the ecteinascidins, the c...

Descripción completa

Detalles Bibliográficos
Autores principales: Kim, Alexia N., Ngamnithiporn, Aurapat, Du, Emily, Stoltz, Brian M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10416225/
https://www.ncbi.nlm.nih.gov/pubmed/37429001
http://dx.doi.org/10.1021/acs.chemrev.3c00054
_version_ 1785087725044498432
author Kim, Alexia N.
Ngamnithiporn, Aurapat
Du, Emily
Stoltz, Brian M.
author_facet Kim, Alexia N.
Ngamnithiporn, Aurapat
Du, Emily
Stoltz, Brian M.
author_sort Kim, Alexia N.
collection PubMed
description [Image: see text] The tetrahydroisoquinoline (THIQ) natural products constitute one of the largest families of alkaloids and exhibit a wide range of structural diversity and biological activity. Ranging from simple THIQ natural products to complex trisTHIQ alkaloids such as the ecteinascidins, the chemical syntheses of these alkaloids and their analogs have been thoroughly investigated due to their intricate structural features and functionalities, as well as their high therapeutic potential. This review describes the general structure and biosynthesis of each family of THIQ alkaloids as well as recent advancements of the total synthesis of these natural products from 2002 to 2020. Recent chemical syntheses that have emerged harnessing novel, creative synthetic design, and modern chemical methodology will be highlighted. This review will hopefully serve as a guide for the unique strategies and tools used in the total synthesis of THIQ alkaloids, as well as address the longstanding challenges in their chemical and biosynthesis.
format Online
Article
Text
id pubmed-10416225
institution National Center for Biotechnology Information
language English
publishDate 2023
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-104162252023-08-12 Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020) Kim, Alexia N. Ngamnithiporn, Aurapat Du, Emily Stoltz, Brian M. Chem Rev [Image: see text] The tetrahydroisoquinoline (THIQ) natural products constitute one of the largest families of alkaloids and exhibit a wide range of structural diversity and biological activity. Ranging from simple THIQ natural products to complex trisTHIQ alkaloids such as the ecteinascidins, the chemical syntheses of these alkaloids and their analogs have been thoroughly investigated due to their intricate structural features and functionalities, as well as their high therapeutic potential. This review describes the general structure and biosynthesis of each family of THIQ alkaloids as well as recent advancements of the total synthesis of these natural products from 2002 to 2020. Recent chemical syntheses that have emerged harnessing novel, creative synthetic design, and modern chemical methodology will be highlighted. This review will hopefully serve as a guide for the unique strategies and tools used in the total synthesis of THIQ alkaloids, as well as address the longstanding challenges in their chemical and biosynthesis. American Chemical Society 2023-07-10 /pmc/articles/PMC10416225/ /pubmed/37429001 http://dx.doi.org/10.1021/acs.chemrev.3c00054 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Kim, Alexia N.
Ngamnithiporn, Aurapat
Du, Emily
Stoltz, Brian M.
Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020)
title Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020)
title_full Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020)
title_fullStr Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020)
title_full_unstemmed Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020)
title_short Recent Advances in the Total Synthesis of the Tetrahydroisoquinoline Alkaloids (2002–2020)
title_sort recent advances in the total synthesis of the tetrahydroisoquinoline alkaloids (2002–2020)
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10416225/
https://www.ncbi.nlm.nih.gov/pubmed/37429001
http://dx.doi.org/10.1021/acs.chemrev.3c00054
work_keys_str_mv AT kimalexian recentadvancesinthetotalsynthesisofthetetrahydroisoquinolinealkaloids20022020
AT ngamnithipornaurapat recentadvancesinthetotalsynthesisofthetetrahydroisoquinolinealkaloids20022020
AT duemily recentadvancesinthetotalsynthesisofthetetrahydroisoquinolinealkaloids20022020
AT stoltzbrianm recentadvancesinthetotalsynthesisofthetetrahydroisoquinolinealkaloids20022020